Run Your DIY Music Career Like A Tech Start-up

George Paolini and Sherry-Lynn Lee of indie duo 23rd Hour have a unique perspective that straddles music and tech—two different worlds that have a lot to teach each other. In addition to making music, Sherry co-founded a start-up and works in tech in Silicon Valley. George is a former exec with Sun Microsystems, HP and Cisco.

“I say luck is when an opportunity comes along and you’re prepared for it.”—Denzel Washington

By George Paolini & Sherry-Lynn Lee of 23rd Hour, a jazz-influenced singer-songwriter duet from Silicon Valley

Pop stars and geeky Silicon Valley celebrities have one thing in common: They got lucky overnight.

But were they lucky? And was it overnight?

Maybe they were in the right place at the right time. But, no doubt, behind the scenes, in either profession, there was a lot of hard work, diligence, perseverance, focus, passion, and drive.

As musicians working and living in Silicon Valley, we’re in a pretty good place to make the comparison between the two worlds of entertainment and technology.

We work in the tech industry. But every other available hour is spent on our music. Having just released our first album, we can tell you that the process is a lot less like the brilliant parody “Spinal Tap” and a lot more like a start-up getting its first app out the door.

Both tech and music require the same drive, the same 24/7 obsession.

We can speak from experience on this. Having just launched our first album, the amount of work it took to produce this product was mind-boggling and sometimes overwhelming. Not much different than a start-up. We started each morning at the kitchen table with laptops opened and ended in the same spot at night before going to bed.

Both need a long-term strategy to be more than a one-hit wonder.

The fun doesn’t stop after the release is out, whether it’s music or a new software app. In fact, the workload seems to increase as you look for ways to get your product “adopted.” We had the good fortune of making it on to the iTunes Jazz charts at № 31. Rather than sit back and soak in the sunshine of success, we immediately went to work to get to № 10. We are constantly looking for new ways to promote our album and already starting work on the next.

Both must differentiate to cut above the noise.

When you have a commodity product (music or software apps), you have to distinguish yourself in other ways. An app provider might do so with better customer service or a unique feature. For music, it’s about making the audience feel special.

We happen to believe in music in schools. We came up with a way to support our cause and, in turn, to harness this interest as a way to set ourselves apart from the crowd of other music offerings. We donated proceeds from our launch gig and our first week’s album sales to charity. Fans appreciated getting involved and helping a worthy charity in the process.

Both must find a niche of early adopters that can propel them to the next level.

For the tech world, it’s about beta testers. More often than not, the early adopters of a new gadget or app become its most vociferous proponents. Just ask any Tesla owner what they think about their ride (if they haven’t already told you without your asking).

In the world of DIY music, it’s about your fans and there is no better way to engage them than in person. But that doesn’t “scale,” as they say in the tech world. The way to reach a wider audience is through social media and email. And of those, email is by far the most effective at a personalized touch.

We built an email database of 1,500 names. That’s a lot by DIY music standards. But rather than blast out the same message to all 1,500, we decided to tailor the message based on demographics, geographics and other segmentations that could provide a more engaging message. The result was that we had a 3X higher than average open rate and a 2X higher click- through rate. But perhaps even more significantly, people emailed us back! The message resonated.

Both must be wary of the abundance of self-proclaimed experts willing to “help” them for “equity” or upfront cash.

In the tech world, start-ups try to self-fund as long as they can to preserve their equity. Ultimately they will need to bring in outside capital. But unlike the dot-com boom, they are much more reluctant to just give away the store.

In the music industry, there might be agents, managers, promoters or even labels that want to “help.” Our experience with tech made us cautious and we believe we were better off because of it. We can’t tell you the number of promoters who called with great offers to play a particular venue. Upon further investigation, we would have had to “pay to play,” and so we politely declined. There were others that had special services (for a modest fee, of course) such as distributing our music videos. The details were always sketchy and, hence, we said “no thanks.”

Both will hire people to help them at various points for things that are outside their areas of expertise.

When you do take on outside help, you’ll learn that it is more work than if you did it yourself. But they are the experts in their field (PR, marketing, legal, financial, etc.) and are much more effective at what they do.

By being organized and thorough, you can provide them the information at a level of detail that will make them more successful in their area of discipline. And that will ultimately help you be more successful.

Both have had their markets completely turned upside down in the past decade.

It used to be we purchased big applications on DVDs at a Best Buy type of big box store. Sales then moved online and were abruptly decomposed into smaller “apps” (even the name got shortened). Now, it’s all about “software as a service” (i.e. rented and streaming).

Music has gone from CD sales to online downloads to online streaming in what seems like overnight. And just as apps have gotten smaller, music has been disaggregated. It used to be that you purchased an entire album (and usually listened to it in order). Now, of course, you can buy any song from any album or create any playlist your little heart desires.

Both must navigate the murky waters of “freemium” vs. premium offerings.

Nobody, it seems, wants to pay for anything anymore. Both music and software are as vulnerable as any two industries to this phenomenon. Online app stores offer limited capabilities for free with annoying ads that practically drive you to spend the $1.99 for an upgrade. The music industry isn’t much different: Streaming services bombard you with commercial offerings until you upgrade.

We offer our album for sale or streaming, but we offer free songs (can be an alternate take or high-quality demo) to our fanbase as a way to keep them engaged.

So those are just a few examples of how these two industries are very similar. If you’re thinking about what it takes to launch an album, your best example might not be to look to your favorite singer-songwriter or band as a model but might very well be to study the two geeks in a garage creating the next killer app with the funny name.

23rd Hour is a jazz-influenced singer-songwriter duet from Silicon Valley, composed of George Paolini & Sherry-Lynn Lee. Sherry co-founded a start-up and currently works in tech in Silicon Valley. George is a former executive with Sun Microsystems, HP, Cisco and has worked at or consulted for numerous start-ups in the Bay Area. Their album “Perfect Strangers” is now available on all platforms, including for free streaming on their website: 23rdhr.com

At this time in my life, I'm finally able to express myself through jazz as I have always wanted by becoming fully immersed in the music and lyrics. I love performing American Jazz
Standards and surrounding myself with world class musicians

At this time in my life, I'm finally able to express myself through jazz as I have always wanted by becoming fully immersed in the music and lyrics. I love performing American Jazz
Standards and surrounding myself with world class musicians. There is no other feeling as fulfilling as performing jazz.